Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
  • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
  • C09K19/2021—Compounds containing at least one asymmetric carbon atom

Definitions

• This invention relates to the optically active aromatic compounds represented by the formula (I): (wherein X represents -COO- or -OCO-; Y represents -COO-, -OCO- or -O-; R 2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms optionally substituted by halogen atoms; R 1 represents an alkyl group having 3 to 20 carbon atoms; Z represents wherein P represents a number of 1 to 5 and * indicates asymmetric carbon atom; and k each represents a number of 1 or 2; m and s each represents a number of 0 or 1), preparation processes therefor, liquid crystal materials containing such aromatic compounds as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.
• formula (I) (wherein X represents -COO- or -OCO-; Y represents -COO-, -OCO- or -O-; R 2 represents an alkyl or alkoxyalkyl group having
• optically active aromatic compounds represented by the formula (I) are the novel compounds found out for the first time by the present inventors. These compounds are useful as liquid crystal compounds, especially ones showing excellent responsiveness in video display. Further, the compounds of this invention can be worked into liquid crystal compositions that can be utilized as a liquid crystal element for producing a light switching element.
• liquid crystal compounds When the term “liquid crystal compounds” is used in this specification, it means not only those compounds which are per se capable of forming a liquid crystal phase but also the compounds which are useful as a component to be blended for a liquid crystal even if they per se cannot be observed as a liquid crystal phase.
• Image display devices utilizing liquid crystal are now widely provided for practical application, and particularly, TN (twisted nematic) type display system is popularly employed for such devices.
• This system had many advantages such as small power consumption and softness to the eye because of the light-receiving type display panel which itself is not liminous, but on the other hand it has the defect that the response speed in image display is low.
• This system utilizes chiral smectic phases such as chiral smectic C phase which shows ferroelectricity (hereinafter referred to as "Sc * "). It is known that not only the Sc * , but also chiral smectic F, G, H, and I phases show ferroelectricity.
• Ferroelectric liquid crystals to be used for actually used ferroelectric liquid crystal display devices are required to have many characteristics. However, at present these requirements cannot be satisfied by only one compound and ferroelectric liquid crystal compositions obtained by mixing some liquid crystal compounds or non-liquid crystal compounds must be used for satisfying them.
• Such ferroelectric liquid crystal compositions may be not only those which comprise only ferroelectric liquid crystal compounds.
• Japanese Patent Kokai (Laid-open) No. 61-195187 has reported to obtain ferroelectric liquid crystal compositions by mixing compound or composition which forms non-chiral smectic C, F, G, H, or I phase (hereinafter referred to as "phase such as Sc") as a basic substance with one or more compounds which forms ferroelectric liquid crystal phase, thereby to make the whole a ferroelectric liquid crystal composition.
• phase such as Sc phase such as Sc
• a report has been made to mix a compound or composition which forms a phase such as Sc as a basic substance with one or more compounds which are optically active, but show no ferroelectric liquid crystal phase to make the whole a ferroelectric liquid crystal composition.
• a ferroelectric liquid crystal composition can be produced by mixing a basic substance with one or more compounds which are optically active irrespective of forming ferroelectric liquid crystal phase or not.
• the optically active substance is preferably capable of forming liquid crystal phase and even if it cannot form liquid crystal phase, it is preferably one having structure which resembles a liquid crystal compound, so to speak, a quasi-liquid crystal substance.
• liquid crystal materials which have spontaneous polarization and low viscosity necessary for high speed response and have liquid crystallinity in the lower temperature region.
• the present invention provides a ferroelectric liquid crystal material which has sufficient spontaneous polarization, has high speed responsiveness, has low viscosity and besides has liquid crystallinity in the lower temperature region.
• the present invention provides the optically active aromatic compounds represented by the formula (I): (wherein X represents -COO- or -OCO-; Y represents -COO-, -OCO- or -O-; R 2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms optionally substituted by halogen atoms; R 1 represents an alkyl group having 3 to 20 carbon atoms; Z represents wherein P represents a number of 1 to 5 and * indicates asymmetric carbon atom; and k each represents a number of 1 or 2; m and s each represents a number of 0 or 1), preparation processes therefor, liquid crystal materials containing such aromatic compounds as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.
• formula (I) (wherein X represents -COO- or -OCO-; Y represents -COO-, -OCO- or -O-; R 2 represents an alkyl or alkoxyalkyl group having 1
• optically active aromatic compounds represented by the formula (I) are the liquid crystal compounds presenting a liquid crystal phase which falls in the category of S A phase or Sc * phase.
• the molecules are arranged with an inclination to a specific direction, such direction of inclination being slightly shifted from layer to layer, and a helical structure is observed in molecular orientation (Mol. Cryst. Liq. Cryst., 40, 30 (1977)).
• the Sc * phase is also characterized in that spontaneous polarization takes place in a direction vertical to the axis of said helix.
• the liquid crystal has an optical active group for inducing a helical molecular arrangement at the end of the molecular chain, and that the crystal also has at the end portion of the molecular chain a substituent having a permanent dipole moment in a direction substantially vertical to the major axis of molecule for inducing spontaneous polarization.
• response speed of ferroelectric liquid crystals has correlation with intensity of spontaneous polarization of the liquid crystals and in order to enhance response speed, it is preferred to increase spontaneous polarization.
• the present invention provides liquid crystal compounds having a large polarity and a process for introducing a wide variety of polar groups into liquid crystal compounds.
• optically active aromatic compounds represented by the formula (I) can be produced by reacting phenols represented by the formula (II): (wherein R 1 , Y,l and m have the meanings given above) with optically active carboxylic acids represented by the formula (III): (wherein R 2 , s and Z have the meanings given above; R' represents a hydroxyl group or a halogen atom and k represents a number of 1 or 2), or by reacting carboxylic acid compounds represented by the formula (IV): (wherein R 1 , Y,l and m have the meanings given above and R' represents a hydroxyl group or a halogen atom) with optically active phenols represented by the formula (V): (where R 2 , k, s and Z have the meanings given above).
• optically active carboxylic acids (III) containing asymmetric carbon can be produced, for instance, (In the above reaction formulas, R" represents methyl group, and R' represents hydroxyl group or a halogen atom) (In the above reaction formulas, A represents a protecting group such as tetrahydropyranyl, t-butyldimethylsilyl or benzyl group and R' represents hydroxyl group or a halogen atom.)
• optically active phenols (V) containing asymmetric carbon can be produced, for instance,
• the compounds in which 4-substituted pentyl group in the above compounds is 5-alkoxyhexyl, 5-alkylcarbonyloxyhexyl, 5-alkoxyalkyloxyhexyl, 5-alkoxyalkylcarbonyloxyhexyl, 6-alkoxyheptyl, 6-alkylcarbo- nyloxyheptyl, 6-alkoxyalkyloxyheptyl or 6-alkoxyalkylcarbonyloxyheptyl groups are exemplified. These may also be used as metal phenolates.
• the above alkoxy, alkylcarbonyloxy, alkoxyalkyloxy and alkoxyalkylcarbonyloxy correspond to in the above-mentioned formula (V) and the substituent R 2 is an alkyl group or alkoxyalkyl group of 1-20 carbon atoms which may be substituted with halogen atom and these alkyl group and alkoxyalkyl group are straight chain or branched chain groups. In case of branched chain, this may be an optically active group.
• alkyl group and alkoxyalkyl group are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 1-methylethyl, 1-methylpropyl, 1-methy.lbutyl, 1-methylpentyl, 1-methylhexyl, 1-methylheptyl, 1-methyloctyl, 2-methylethyl, 2-methylbutyl, 2,3-dimethylbutyl, 2,3,3-trimethylbutyl, 2-methylpentyl, 3-methylpentyl, 2,3-dimethylpentyl, 2,4-
• halomethyl, 1-haloethyl, 1-halopropyl, 1-halobutyl, 1-halopentyl, 1-halohexyl, 1-haloheptyl, 1-halooctyl are exemplified.
• substituent R 2 is an optically active group
• substituent R 2 in respect to an atomic group in the formula (V), wherein s is 0, halides or sulfuric acid esters thereof, which are used as an etherification agent in examples of preparing the above-mentioned optically active phenols, can be readily produced from the corresponding optically active alcohols.
• Some of said optically active alcohols can be obtained from asymmetric reduction of the corresponding ketones.
• optically active amino acids and optically active oxyacids which occur in nature or are obtained by resolution: Alanine, valine, leucine, isoleucine, phenylalanine, serine, threonine, allothreonine, homoserine, alloisoleu- cine, tert-leucine, 2-aminobutyric acid, norvaline, norleucine, ornithine, lysine, hydroxylysine, phenylglycine, trifluoroalanine, aspartic acid, glutamic acid, lactic acid, mandelic acid, tropic acid, 3-hydroxybutyric acid, malic acid, tartaric acid isopropylmalic acid and the like.
• optically active carboxylic acids are used, some of them being obtained by oxidation of the corresponding aminoalcohols or reductive deamination of amino acids. Also, some of others can be derived from the following optically active amino acids and optically active oxyacids which occur in nature or are obtained by resolution:
• Typical examples of said optically active carboxylic acids (III) are (i) 4-(2-alkoxy-1-methyl)ethylbenzoic acid, 4-(2-alkylcarbonyloxy-1-methyl)ethylbenzoic acid, 4-(2-alkoxyalkyloxy-1-methyl)ethylbenzoic acid and 4-(2-alkoxyalkylcarbonyloxy-1-methyl)ethylbenzoic acid, 4-(3-alkoxy-1-methyl)propylbenzoic acid, 4-(4-alkoxy-1-methyl)butylbenzoic acid, 4-(5-alkoxy-1-methyl)pentylbenzoic acid, 4-(6-alkoxy-1-methyl)hexylbenzoic acid.
• 4-(2-alkoxy-I-methyl)ethyl-4'-biphenylcarboxylic acid 4-(2-alkylcarbonyloxy-1-methyl)ethyl-4'-biphenylcarboxylic acid, 4-(2-alkoxyalkyloxy-I-methyl)ethyl-4'-biphenylcarboxylic acid and 4-(2-alkoxyalkylcarbonyloxy-1-methyl)ethyl-4'-biphenylcarboxylic acid.
• optically active carboxylic acids can also be used as acid halides such as acid chloride and acid bromide.
• alkoxy, alkylcarbonyloxy, alkoxyalkyloxy and alkoxyalkylcarbonyloxy correspond to in the above formula (III).
• the substituent R 2 is an alkyl group or alkoxyalkyl group of 1-20 carbon atoms which may be substituted with halogen atom.
• These alkyl group and alkoxyalkyl group are those of straight chain or branched chain and in case of branched chain, this may be an optically active group.
• alkyl group and alkoxyalkyl group are the same as exemplified herebefore.
• phenols (II) and carboxylic acid compounds (IV) used as another starting materials in said reactions are mostly the known compounds and can be produced according to the methods disclosed in the literatures.
• examples of such phenols (II) are 4-alkoxyphenol, 4-alkylphenol, 4'-alkoxy-4-hydroxybiphenyl, 4'-alkyl-4-hydroxybiphenyl, 4-alkoxycarbonylphenol, 4-alkylcarbonyloxyphenol, 4'-alkoxycarbonyl-4-hydroxybiphenyl, 4'-alkylcarbonyloxy- 4-hydroxyphenyl and the like.
• the above alkyl and atkoxy groups have alkyl group of 3-20 carbon atoms and typical examples of the alkyl group are propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl and the like.
• carboxylic acids (IV) mention may be made of, for example, 4-alkoxybenzoic acid, 4-alkylbenzoic acid, 4-'alkoxy-4-biphenylcarboxylic acid, 4'-alkyl-4-biphenylcarboxylic acid, 4-alkoxycarbonylbenzoic acid, 4-alkylcarbonyloxybenzoic acid, 4'-alkoxycarbonyl-4-biphenylcarboxylic acid, 4'-alkylcarbonyloxy-4-biphe- nylcarboxylic acid and the like.
• carboxylic acids can also be utilized as acid halides such as acid chlorides and acid bromides.
• the alkyl and alkoxy in these carboxylic acids have straight chain alkyl group of 3-20 carbon atoms as mentioned above.
• An ordinary esterification method can be applied for the reaction of optically active phenols (V) and carboxylic acid compounds (IV) or the reaction of optically active carboxylic acids (III) and phenols (II), and such reaction can be carried out in the presence or absence of a solvent by using a catalyst.
• such solvent is selected from those which are inert to the reaction, such as aliphatic or aromatic hydrocarbons, ethers, halogenated hydrocarbons and the like, the typical examples thereof being tetrahydrofuran, ethyl ether, acetone, methyl ethyl ketone, toluene, benzene, chlorobenzene, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, dimethylformamide, hexane and the like.
• solvents may be used either singly or in combination. No specific limitations are imposed on the amount of such solvent(s) used.
• optically active phenols (V) and the optically active carboxylic acids (III) used in the reation are expensive, it is advisable to use the other starting material, viz, carboxylic acid compounds (IV) or phenols (II), in an excess amount, usually 1 to 4 equivalents, preferably 1 to 2 equivalents to the optically active phenols (V) or optically active carboxylic acid (III).
• organic or inorganic basic materials such as dimethylaminopyridine, triethylamine, tri-n-butylamine, pyridine, picoline, collidine, imidazole, sodium carbonate, sodium methylate, potassium hydrogencarbonate and the like.
• Organic or inorganic acids such as toluenesulfonic acid, methanesulfonic acid, sulfuric acid, etc., are also usable as catalyst.
• the condensing reagent there can be used organic materials such as N,N'-dicyclohexyl carbodiimide, N-cyclohexyl-N'-(4-diethylamino)cyclohexyl carbodiimide, imidazoylimidazole and the like.
• organic amines such as 4-pyrollidinopyridine, pyridine, triethylamine and the like.
• the amount of a condensing reagent is usually 1 to 1.2 equivalents to the carboxylic acid.
• the amount of the organic amine is usually 0.01 to 0.2 equivalent to a condensing reagent.
• the amount of the catalyst to be used is not specified as it varies depending on the type of the starting materials used, their combination with the catalyst used and other factors, but in case of using an acid halide as a starting material, a basic material is used as catalyst in an amount not less than one equivalent to said acid halide,
• the reaction temperature is usually -30 to 100° C.
• the reaction time is not subject to any specific limitations.
• reaction product is subjected to the ordinary separating means such as extraction, separation of liquid phase, concentration, etc., to isolate the objective optically active aromatic compound of the formula (I). If necessary, the product may be purified by column chromatography, recrystallization or other means.
• optically active aromatic compound to be thus obtained are actually exemplified as follows [In these examples, (C 1-20 ) and (C 3 - 20 ) mean “having 1-20 carbon atoms” and “having 3-20 carbon atom”, respectively].
• alkoxyalkyl and alkyl may be substituted with halogen atom and these alkoxyalkyl and alkyl may be branched alkoxyalkyl and alkyl.
• alkoxyalkyl and alkyl may be optically active alkoxyalkyl and alkyl.
• alkyl and alkoxyalkyl are those as exemplified herebefore (substituent R 2 ).
• X -COO-(ii-1) 4-[2-alkyl(C 1-20 )oxypropyl]phenyl 4-[alkyl(C 3-20 )]benzoate, 4-[2-alkyl(C 1-20 )oxypropylphenyl 4-[alkyl(C 3 -20)oxy]benzoate, 4-[2-alkyl(C 1-20 )oxypropyl]phenyl 4'-[alkyl(C 3 - 20 )-4-biphenylcarboxylate, 4-[2-alkoxy(C 1-20 )-1-methyl]ethylphenyl 4-[alkyl(C 3 - 2o )]benzoic acid ester, 4-[2-alkoxy(C 1-20 )-1-methyl]ethylphenyl 4-[alkyl(C 3 - 2 o)oxy]benzoic acid ester,
• optically active aromatic compound (I) including such compounds as enumerated as above is variable for liquid crystal materials.
• the substituent group R 2 of the general formula (I) is preferably an alkyl or alkoxyalkyl group in view of practical optical stability and the like.
• Compounds, wherein the carbon number of the substituent group R 2 is 1 to 10, are cited as those exhibiting more favorable various physical properties in practical application.
• compounds, wherein the substituent group R 2 having a carbon number of 1 to 10 is an alkoxyalkyl group are more effective in lowering the temperature range of liquid crystals.
• an alkyl group having a carbon number of 8 to 16 is more preferred for practical use, but is not restricted thereto as one component of liquid crystal compositions.
• Compounds, wherein S is 1, have better effects on enhancement of spontaneous polarization values in a ferroelectric liquid crystal phase or in a liquid crystal composition comprising the compounds used as an active component than those of the corresponding compounds, wherein S is 0.
• said optically active aromatic compounds (I) are usually mixed with one or more other types of liquid crystal compounds although said compounds (I) may be used singly.
• liquid crystal compounds to be mixed and their mixing ratio are properly selected according to the purpose of use and not specified.
• Such liquid crystal material can be effectively utilized for producing a light switching element by a known method.
• the novel optically active aromatic compounds represented by the formula (I) can be easily obtained in a high yield.
• These optically active aromatic compounds have very excellent properties as liquid crystal compounds, so that they can be effectively utilized for preparing the liquid crystal materials and the light switching elements can be produced by utilizing such liquid crystal materials.
• reaction mixture was poured into 4N hydrochloric acid and extracted with 200 ml of toluene.
• the organic layer was washed with water, 5% aqueous sodium hydrogencarbonate and water in succession, then dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure.
• the liquid crystal compositions shown in Table 3 were prepared using the liquid crystal compounds. The preparation procedure was that a given compound weighed in a given amount was mixed in a sample bottle, while being heated and molten.
• a polyimide polymeric membrane is further provided on a glass substrate provided with an indium oxid transparent electrode. This is rubbed using a gauze in a certain direction and then a liquid crystal cell is assembled by using glass fibers (a diameter of 5 pm) as a spacer, so as to allow two substrates to be parallel in the rubbing direction.
• the above liquid crystal composition(s) or compound(s) is sealed in vacuo into the liquid crystal cell to obtain a liquid crystal element.
• ferroelectric liquid crystals driven at room temperature can be made when such liquid crystal materials are formed into liquid crystal compositions, even if such materials per se do not exhibit any liquid crystal phase.
• This ferroelectric liquid crystals have been found to posses spontaneous polarization values (P s ) necessary to a high speed response and further to be able to become compound(s) (compositions) having S: phase at a low temperature region.
• reaction mixture was poured into 4N hydrochloric acid and extracted with 200 ml of toluene.
• the organic layer was washed with water, 5% aqueous sodium hydrogencarbonate and water in succession, then dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure.
• the residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain 2.29 g (yield 950/o) of (+ )-4-decyloxybenzoic acid 4-(2-butyryloxypropyl) phenyl ester.
• the liquid crystal compositions shown in Table 5 were prepared using the liquid crystal compounds the preparation procedure was that a given compound weighed in a given amount was mixed in a sample bottle, while being heated and molten.
• a polyimide polymeric membrane is further provided on a glass substrate provided with an indium oxide transparent electrode. This is rubbed using a gauze in a certain direction and then a liquid crystal cell is assembled by using glass fibers (a diameter of 5 ⁇ m) as a spacer, so as to allow two substrates to be parallel in the rubbing direction.
• the above liquid crystal composition(s) or compound(s) is sealed in vacuo into the liquid crystal cell to obtain a liquid crystal element.
• ferroelectric liquid crystals driven at room temperature can be made when such liquid crystal materials are formed into liquid crystal compositions, even if such materials per se do not exhibit any liquid crystal phase.
• This ferroelectric liquid crystals have been found to posses spontaneous polarization values (Ps) necessary to a high speed response and further to be able to become compounds(s) (compositions) having S: phase at a low temperature region.
• reaction mixture was poured into 4N hydrochloric acid and extracted with 200 ml of toluene.
• the organic layer was washed with water, 50/o aqueous sodium hydrogencarbonate and water in succession, then dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure.
• the residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain 2.38 g (yield 96%) of (+)-4-decyloxybenzoic acid 4-(3-butyryloxybutyl)phenyl ester.
• the liquid crystal compositions shown in Table 7 were prepared using the liquid crystal compounds. The preparation procedure was that a given compound weighed in a given amount was mixed in a sample bottle, while being heated and molten.
• a polyimide polymeric membrane is further provided on a glass substrate provided with an indium oxid transparent electrode. This is rubbed using a gauze in a certain direction and then a liquid crystal cell is assembled by using glass fibers (a diameter of 5 ⁇ m) as a spacer, so as to allow two substrates to be parallel in the rubbing direction.
• the above liquid crystal composition(s) or compound(s) is sealed in vacuo into the liquid crystal cell to obtain a liquid crystal element.
• ferroelectric liquid crystals driven at room temperature can be made when such liquid crystal materials are formed into liquid crystal compositions, even if such materials per se do not exhibit any liquid crystal phase.
• This ferroelectric liquid crystals have been found to posses spontaneous polarization values (P s ) necessary to a high speed response and further to be able to become compound(s) (compositions) having S: phase at a low temperature region.
• reaction mixture was poured into 4N hydrochloric acid and extracted with 200 ml of toluene.
• the organic layer was washed with water, 50/o aqueous sodium hydrogencarbonate and water in succession, then dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure.
• the residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain 2.45 g (yield 96%) of (+)-4-decyloxybenzoic acid 4-(4-butyryloxypentyl)phenyl ester.
• Phase transition temperature and value of spontaneous polarization of the compounds obtained in Table 9 are shown in Table 10 (The values of spontaneous polarization are those measured by using liquid crystal element prepared by the method of preparation of liquid crystal elements hereinafter stated.).
• the liquid crystal compositions shown in Table 11 were prepared using the liquid crystal compounds. The preparation procedure was that a given compound weighed in a given amount was mixed in a sample bottle, while being heated and molten.
• a polyimide polymeric membrane is further provided on a glass substrate provided with an indium oxid transparent electrode. This is rubbed using a gauze in a certain direction and then a liquid crystal cell is assembled by using glass fibers (a dimeter of 5 ⁇ m) as a spacer, so as to allow two substrates to be parallel in the rubbing direction.
• the above liquid crystal composition(s) or compound(s) is sealed in vacuo into the liquid crystal cell to obtain a liquid crystal element.
• ferroelectric liquid crystals can be made when such liquid crystal materials are formed into liquid crystal compositions, even if such materials per se do not exhibit any liquid crystal phase.
• the liquid crystal materials shown in Table 12 are sealed in the liquid crystal elements prepared by the method of preparation of liquid crystal elements in Example 130 and are measured respectively in the spontaneous polarization. The results are given in Table 12.

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